(3S,4R)-8-hydroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-isochromene-7-carboxylic acid | 112245-94-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (3S,4R)-8-hydroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-isochromene-7-carboxylic acid
• 英文别名: (3S,4R)-6-hydroxy-3,4,5-trimethyl-8-oxo-3,4-dihydroisochromene-7-carboxylic acid
• CAS: 112245-94-0
• 化学式: C₁₃H₁₄O₅
• 分子量: 250.25
• InChiKey: CBGDIJWINPWWJW-FSPLSTOPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

ADMET

代谢

在查尔斯河CD-1大鼠妊娠第12天进行皮下注射后，14C-桔霉素跨越了胎盘。... 对母体血浆提取物的母体血浆提取物进行高效液相色谱分析，揭示了母体化合物和至少一个未识别的代谢物的存在，该代谢物比母体化合物更具极性；在尿液中至少发现了两个未识别的代谢物。母体胆汁样本的色谱图表明，除了母体化合物外，还存在至少一个代谢物，而胎儿提取物中仅含有母体化合物。

Following subcutaneous injection on day 12 of gestation, 14C-citrinin crossed the placenta in Charles River CD-1 rats. ... High-performance liquid chromatography of maternal plasma extracts revealed the presence of the parent compound and at least one unidentified metabolite, which was more polar than the parent compound; at least two unidentified metabolites were found in urine. Chromatograms of maternal bile samples suggested the presence of at least one metabolite, apart from the parent compound, whereas fetal extracts contained only the parent compound.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

没有关于人类的数据可用。动物致癌性的证据有限。总体评估：第3组：该物质对人类致癌性不可分类。

No data are available in humans. Limited evidence of carcinogenicity in animals. OVERALL EVALUATION: Group 3: The agent is not classifiable as to its carcinogenicity to humans.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌物分类

国际癌症研究机构致癌物：橘青霉素

IARC Carcinogenic Agent:Citrinin

来源:International Agency for Research on Cancer (IARC)

毒理性

• 致癌物分类

国际癌症研究机构（IARC）致癌物分类：第3组：对其对人类的致癌性无法分类

IARC Carcinogenic Classes:Group 3: Not classifiable as to its carcinogenicity to humans

来源:International Agency for Research on Cancer (IARC)

毒理性

• 致癌物分类

国际癌症研究机构专论：第40卷：（1986年）一些天然存在和合成的食品成分，呋喃香豆素和紫外线辐射

IARC Monographs:Volume 40: (1986) Some Naturally Occurring and Synthetic Food Components, Furocoumarins and Ultraviolet Radiation

来源:International Agency for Research on Cancer (IARC)

毒理性

• 相互作用

短叶菌素抑制了烟草花叶病毒接种的N. glutinosa叶片上的局部病变诱导。它在温度变化后4小时或2小时内施用于叶片。

Citrinin inhibited local lesion induction on N. glutinosa leaves inoculated with tobacco mosaic virus. It was applied on leaves within 4 or 2 hr after the temp shift.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

在大鼠肾皮质切片中... 14C-Citrinin的摄取被乳酸增强，并被丙苯酸（一种特定的阴离子运输抑制剂）所减少。二硝基苯酚是一种代谢抑制剂，也是阴离子运输的竞争性抑制剂，它也减少了Citrinin的运输。有机阳离子并未改变切片中Citrinin的积累。这些数据与Citrinin通过肾脏有机阴离子分泌系统的运输是一致的。

/In/ Rat renal cortical slices ... 14C-Citrinin uptake was enhanced by lactate and reduced by probenecid, a specific inhibitor of anion transport. Dinitrophenol is a metabolic inhibitor as well as competitive inhibitor of anion transport, and it also reduced citrinin transport. Organic cations did not alter citrinin accumulation by the slices. These data are consistent with the transport of citrinin by the renal organic anion secretory system.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

在大鼠静脉给药后0.5小时，观察到标记化合物14C的总放射性在肝脏和肾脏中分别为14.7%和5.6%，到6小时时，肝脏中降至7.5%，肾脏中降至4.7%。血浆中(14)C的浓度从0.5小时时的9.2%下降到6小时时的4.7%。血浆的半衰期分别为2.6小时和14.9小时。大约80%在24小时内通过粪便和尿液排出。第二组大鼠在给药3毫克/公斤(14)C-桔霉素之前4天，预先腹腔注射50毫克/公斤的桔霉素。尿液排出量增加。血浆消失曲线有两个消除速率，半衰期分别为0.6小时和14.1小时。肾毒性大鼠在示踪剂剂量后24小时内，在肝脏中保留了7.5%的给药放射性，而恢复的大鼠为1.3%；72小时后，47%的(14)C通过粪便或结肠内容物排出，而恢复的大鼠为17.5%。在正常大鼠中，肾脏显然是主要的消除途径。

0.5 hr after iv administration of (14)C-labeled compound to rats, 14.7% & 5.6% of total radioactivity were observed in liver & kidneys respectively, & by 6 hr decreased to 7.5% in liver & 4.7% in kidney. Plasma concentration of (14)C decreased from 9.2% at 0.5 hr to 4.7% at 6 hr. Plasma /half-lives/ were 2.6 & 14.9 hr. Approx 80% was excreted in feces & urine by 24 hr. A 2nd group was pretreated with 50 mg/kg citrinin, ip, 4 days prior to administration of 3 mg/kg (14)C-citrinin, iv. Urine output was enhanced. Plasma disappearance curve had 2 elimination rates, with /half-lives/ of 0.6 & 14.1 hr. Nephrotoxic rats retained 7.5% of the administered radioactivity in liver compared to 1.3% in recovered rats 24 hr after tracer dose & 47% of (14)C was excreted in feces or in colon contents after 72 hr compared to 17.5% in recovered rats. In normal rats the kidneys apparently are major route of elimination.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

柑橘素（25-50 mg/kg）据报道在大鼠的胃肠道和猫的口腔吸收不良。

Citrinin (25-50 mg/kg) has been reported to be poorly absorbed from the gastrointestinal tract of rats and from the mouth of cats.

来源:Hazardous Substances Data Bank (HSDB)